CN110483528A - A kind of novel phosphorescence host compound and the electroluminescent device using the compound - Google Patents

A kind of novel phosphorescence host compound and the electroluminescent device using the compound Download PDF

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CN110483528A
CN110483528A CN201910747927.4A CN201910747927A CN110483528A CN 110483528 A CN110483528 A CN 110483528A CN 201910747927 A CN201910747927 A CN 201910747927A CN 110483528 A CN110483528 A CN 110483528A
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compound
independently selected
unsubstituted
phosphorescence host
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汪华月
华万鸣
申屠晓波
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Zhejiang Hua Hui Photoelectric Technology Co Ltd
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Abstract

The invention discloses a kind of novel phosphorescence host compound and using the electroluminescent device of the compound, the organic compound is as shown in structural formula I:In structural formula I, L1、L2Independent to be selected from singly-bound, phenylene, naphthylene, Z is independently selected from H, C6-C30 aryl, C2-C30 heteroaryl；X is independent to be selected from O, S, Se, NR1、C(R1)2、Si(R1)2, wherein R1Independently selected from hydrogen, C1-C20 alkyl substituted or unsubstituted, C1-C20 alkoxy substituted or unsubstituted, C6-C30 aryl or C2-C30 heteroaryl.Phosphorescence host compound of the invention has preferable thermal stability, in HOMO, LUMO of dopant can be enclosed in by deeper HOMO and shallower LUMO, the transmitting of hole and electronics can be balanced, energy transmission is more abundant, can effectively improve efficiency and the service life of device.

Description

A kind of novel phosphorescence host compound and the electroluminescent device using the compound
Technical field
The present invention relates to a kind of field of organic electroluminescence, specially a kind of novel phosphorescence host compound and use the change Close the electroluminescent device of object.
Background technique
The luminous of OLED belongs to electroluminescence (eletro luminescence EL), due to applying upper importance, Electroluminescence phenomenon is always interesting a science, and organic light emission phenomenon is to be sent out by pope professor for 1963 earliest Existing, the bias of hundreds of volts was applied on anthracene (anthracene) crystal by he at that time, observed luminescence phenomenon, this is earliest Document report.Due to excessively high voltage and bad luminous efficiency, which is not affected by always attention.Until 1987, beauty Multiple field has been made in doctor Deng Qingyun (chingW.Tang) of Kodak, state and Steve publication in a manner of vacuum evaporation OLED device, but the interface accessory that hole is confined to electron transfer layer and hole transmission layer with electronics is combining, significantly Improve the performance of device, the business application potentiality of operating voltage and high brightness have attracted the sight in the whole world, open from this The epoch that OLED surges forward.OLED, which shines, is divided into fluorescence radiation and the luminous two ways of phosphorescence, is speculated according to theory, by charge The singlet excited caused by combination and triplet excited state ratio be 1:3, so the use of small molecule fluorescent material being energy It is only the 25% of whole energy for what is shone, remaining 75% energy loses because of the non-luminescent mechanism of triplet excited state Fall, therefore is generally acknowledged that the internal quantum limit of fluorescent material is 25%.The human hairs such as Baldo and Forrest professor in 1998 Existing triplet state phosphorescence can utilize at room temperature, and the upper limit of original internal quantum efficiency be promoted to 100%, triplet phosphorescence Body is all usually heavy metal atom, and the complex compound of composition, using heavy atoms effect, strong spin orbital coupling causes list The energy rank of weight excitation state and triplet excited state is mutually mixed, so that forbidden triplet energies are alleviated in the form of phosphorescence originally It shines, quantum efficiency is also substantially improved therewith, and the luminescent layer almost all in current organic OLED component is shone using Subjective and Objective Architecture adulterates guest emitting material in host emitter, in general, main body shine can be need to be bigger than dopant, I.e. energy passes to object by theme, and dopant is made to be excited and shine.
Blue phosphorescent system stops at laboratory stage due to short-lived reason at present, and green light and feux rouges phosphorescence are mixed Miscellaneous system has been successfully applied to commercial field, such as mobile phone, illumination and large size TV field, so it is red how to improve green light The luminous efficiency of light phosphorescent emitter system has been now subjected to attracting attention for industry, and most successful no more than Premix motif material Develop and utilize, principle be using the p-type material and strong electron injection of strong hole injection n type material different proportion it is mixed It closes, causes hole and electron trap in luminescent layer, to improve the luminous efficiency of material, but need to require p-type main body and N-type Main body has identical vapor deposition temperature, and p-type material of main part and the material proportion of N-type main body are deposited for a long time will not change, this is serious Limit the development of premix material of main part.
Summary of the invention
The purpose of the present invention is to provide a kind of novel phosphorescence host compound, the structures of the phosphorescence host compound Formula is as shown in structural formula I:
Structural formula I,
Wherein, L1、L2It is independent to be selected from singly-bound, phenylene, naphthylene；
Z is independently selected from H, C6-C30 aryl, C2-30 heteroaryl；
X is independent to be selected from O, S, Se, NR1、C(R1)2、Si(R1)2, wherein R1Independently selected from hydrogen, C1-C20 substituted or unsubstituted Alkyl, C1-C20 alkoxy substituted or unsubstituted, C6-C30 aryl or C2-C30 heteroaryl.
Preferably, the phosphorescence host compound, Z is independently selected from substituted or unsubstituted following knot in structural formula I Structure:
Wherein, R2、R3、R4Independently selected from hydrogen, C1-C20 alkyl substituted or unsubstituted, C1-C20 alkoxy substituted or unsubstituted, C6-C30 aryl or C2-C30 heteroaryl；
Y1、Y2、Y3Independently selected from C or N.
Preferably, the phosphorescence host compound, it is characterised in that: the C6-C30 aryl is selected from phenyl, naphthalene, connection One of phenyl, terphenyl and phenanthryl.
Preferably, the phosphorescence host compound, it is characterised in that: the C2-C30 heteroaryl is selected from pyridyl group, connection One of pyridyl group, quinolyl, isoquinolyl, phenanthroline and triazine radical.
Preferably, the phosphorescence host compound, it is characterised in that: the R1Independently selected from flowering structure:
As a kind of further preferred, novel change of the phosphorescence host compound independently selected from following structural of the present invention Close object:
The present invention also provides a kind of organic electroluminescence device, which includes cathode layer, anode layer and organic layer, is somebody's turn to do Organic layer includes hole injection layer, hole transmission layer, luminescent layer, hole blocking layer, CPL layers, electron injecting layer, electron transfer layer In it is one or more layers, wherein in organic layer at least one layer contain compound as described in structural formula I.
Wherein, phosphorescence host compound described in structural formula I is as previously described.
Further, phosphorescence of the phosphorescence host compound as organic electroluminescence device luminescent layer described in structural formula I Material of main part.
Compound described in structural formula I can be used alone, or be used in mixed way with other compounds；As described in structural formula I Compound one of compound can be used, can also be simultaneously using two or more compound in structural formula I.
Beneficial effects of the present invention:
1. the novel phosphorescence host compound molecular weight of the present invention is bigger, empty by singly linked multiple conjugate planes groups Between symmetry it is poor, be not easy crystallization decompose, improve the glass transition temperature of material, ensure that material over time vapor deposition be not decomposed；
2. organic compound of the invention is applied to the luminescent layer in OLED device, and uses as material of main part, the present invention has Deeper HOMO and shallower LUMO can be enclosed in the inside with the HOMO of RD (dopant), LUMO, and energy transmission is more abundant；
3. organic compound of the invention is applied to electroluminescent device as phosphorescent light body material, there is biggish T1 can hinder Exciton diffusion is kept off, efficiency and the service life of device are improved；
4. Phosphorescent host compound of the invention can balance the transmitting of hole and electronics, the service life of device is improved.
Detailed description of the invention
Fig. 1 is a kind of organic electroluminescent diode apparatus structure sheaf figure of the present invention.
Specific embodiment
The present invention provides a kind of phosphorescence host compound, the structural formula of the phosphorescence host compound such as structural formula I It is shown:
Structural formula I
Wherein, L1、L2It is independent to be selected from singly-bound, phenylene, naphthylene；
Z is independently selected from H, C6-C30 aryl, C2-30 heteroaryl；
X is independent to be selected from O, S, Se, NR1、C(R1)2、Si(R1)2, wherein R1Independently selected from hydrogen, C1-C20 substituted or unsubstituted Alkyl, C1-C20 alkoxy substituted or unsubstituted, C6-C30 aryl or C2-C30 heteroaryl.
Preferably, the phosphorescence host compound, Z is independently selected from substituted or unsubstituted having structure in structural formula I:
Wherein, R2、R3、R4Independently selected from hydrogen, C1-C20 alkyl substituted or unsubstituted, C1-C20 alkoxy substituted or unsubstituted, C6-C30 aryl or C2-C30 heteroaryl；
Y1、Y2、Y3Independently selected from C or N.
Preferably, the phosphorescence host compound, it is characterised in that: the C6-C30 aryl is selected from phenyl, naphthalene, connection One of phenyl, terphenyl and phenanthryl.
Preferably, the phosphorescence host compound, it is characterised in that: the C2-C30 heteroaryl is selected from pyridyl group, connection One of pyridyl group, quinolyl, isoquinolyl, phenanthroline and triazine radical.
Preferably, the phosphorescence host compound, it is characterised in that: the R1Independently selected from flowering structure:
Further preferred embodiment, compound of the phosphorescence host compound independently selected from following structural of the present invention:
The present invention also provides a kind of electroluminescent device, including cathode layer, anode layer and organic layer, which includes Hole injection layer, hole transmission layer, luminescent layer, hole blocking layer, CPL layers, one layer in electron injecting layer, electron transfer layer or One layer or more, it is characterised in that: contain the compound as described in structural formula I at least one layer in the organic layer of the device.
In a kind of electroluminescent device of the present invention, compound described in structural formula I is used as phosphorescence in luminescent layer Material of main part.
In a kind of electroluminescent device of the present invention, compound described in structural formula I be can be used alone, or and Other compounds are used in mixed way；It can also be simultaneously using two or more compound in structural formula I；Phosphorescence host compound 1-36 can be separately as the phosphorescent light body material of device luminescent layer, can also be simultaneously using two or more work in 1-36 For the phosphorescent light body material of device luminescent layer.
In order to make the objectives, technical solutions, and advantages of the present invention clearer, below in conjunction with specific embodiment, to this Invention is further elaborated.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, not For limiting the present invention.
Synthesis example
Embodiment 1: the synthesis of compound 4
1, the synthesis of intermediate Sub-1
Under nitrogen protection, 3- amino -2- indenes formonitrile HCN (23.27g, 149mmol), tetrahydrofuran (200mL) are added in there-necked flask Stirring later, phenyl-magnesium-bromide is added dropwise, and (87.4mL, 3.0mol/L, solvent are Et2O) and mixture is small in 0 DEG C of stirring 1 When.Ethyl chloroformate (19.4g, 179mmol) is added dropwise and flows back about 1 hour.Solution is adjusted with ammonium chloride until becoming micro- Acidity, and with water and heptane wash, obtain intermediate [Sub-1] 34.37g (yield 80%).The compound of generation is by using LC- MS is determined.Mass spectrum m/z, theoretical value: 288.34；Measured value: 288.13.Theoretical elemental content (%) C19H16N2O:C, 79.14； H,5.59；N,9.72；O,5.55.
2, the synthesis of intermediate Sub-2
Under nitrogen protection, [Sub-1] (31.71g, 110mmol) is added in there-necked flask to be placed in about 80mL chlorosulfuric acid, flowed back Night after being cooled to -20 DEG C, is slowly added to distilled water to about 400mL.With water, methanol and heptane wash, and in toluene and heptane Recrystallization, obtains intermediate Sub-2 (15.18g, yield 45%).The compound of generation with LC-MS by being determined.Mass spectrum m/z, Theoretical value: 306.79；Measured value: 306.09.Theoretical elemental content (%) C19H15CLN2: C, 74.38； H,4.93；CL, 11.56；N,9.13.
3, the synthesis of compound 4
Under a nitrogen atmosphere, 9'- phenyl -9H, 9H'-3,3'- carbazole (0.22g, 0.52mmol) is added in three-necked flask, Sub-2 (0.98g, 0.63mmol)、Cu(OTf)2(0.04g) and potassium carbonate (0.27g, 0.87mmol), is then added trichloro-benzenes (25g) is heated to 210 DEG C or so under mechanical stirring and is refluxed overnight, and stops heating after fully reacting, and vacuum distillation removes molten Agent obtains compound 4 (0.23g, yield 81.0%) with silica gel column chromatography.The compound of generation with LC-MS by being determined.Mass spectrum M/z, theoretical value: 678.82；Measured value: 678.28.Theoretical elemental content (%) C49H34N4: C, 86.70；H,5.05；N,8.25.
Embodiment 2: the synthesis of compound 5
With the synthetic method in embodiment 1, compound 5 is obtained.The compound of generation with LC-MS by being determined.Mass spectrum m/z, reason By value: 678.82；Measured value: 678.29.Theoretical elemental content (%) C49H34N4: C, 86.70；H,5.05；N,8.25.
Organic compound of the invention is applied in OLED luminescent device, is used as phosphorescent light body material, is had higher Triplet, can be improved luminous efficiency and the service life of device.The survey of physical property has been carried out to the compounds of this invention 4,5 Fixed, testing result is as shown in table 1.
Table 1
Note: HOMO is measured by Hitachi, Japan AC2, and Eg is calculated by UV λ onset, and S1 is calculated by transmitting wave crest, UV It is to be measured by Shanghai Ke Qi UV1700 ultraviolet-uisible spectrophotometer, PL is measured by Japanese Shimadzu emission spectrometer PDA-7000.
It is each that the present invention is also prepared for 2 red top illuminating devices (4/ compound 5 of compound) by way of hot evaporation Specific device architecture is as follows:
Device embodiments 3:
Its preparation step includes:
A. it cleans the transparent top OLED fluorescent glass substrate and uses deionized water, acetone, isopropanol ultrasonic cleaning 15min respectively, 80 DEG C drying 1h, investment vapor deposition chamber, plasma treatment anode surface；
B. hole injection layer material HT1:NDP-9 (10nm:0.3) is deposited by way of hot evaporation in anode surface
C. it is deposited by way of hot evaporation HT1 (1200nm), which is hole transmission layer；
D. RPrime (800nm) is deposited in hole transport layer surface, this layer is the buffer layer of luminescent layer and hole transmission layer；
E. compound 4 and RD (40nm:0.3) are deposited by way of hot evaporation, which is luminescent layer；
F. HBL1 (5nm) is deposited in luminous layer surface, which is hole transmission layer；
G. ET1 and LiQ (15nm:15) is deposited in HBL1 layer surface, which is ETL layers；
H. Ag, Mg (12nm:1.2) layer is deposited as cathode in hot evaporation mode in ETL layer surface；
I. one layer CPL layers are deposited in cathode surface, which mainly improves light extraction efficiency；
After completing electroluminescent device according to above-mentioned steps, the current efficiency of measurement device and service life, the current versus brightness-of device Voltage characteristic is the source the Keithley measuring system (Keithley 2400 by having corrected silicon photoelectric diode Sourcemeter, Keithley 2000Currentmeter) complete, electroluminescent spectrum is by French JY company SPEX CCD3000 spectrometer measurement, all measurements are completed in atmosphere at room temperature.Relevant molecular structure is shown below:
Device embodiments 4: preparation step is with embodiment 3, and only luminescent layer material of main part replaces with as compound 5；
Device comparative example: preparation step is with embodiment 3, and only luminescent layer material of main part replaces with as compound R H35；
The detection data of gained electroluminescent device is shown in Table 2.
Table 2
Phosphorescence host luminescent material of the invention as shown in Table 2, luminous efficiency reach 40cd/A or more, and luminescent color is dark red, energy It is successfully applied to OLED display field.
The foregoing is only a preferred embodiment of the present invention, but scope of protection of the present invention is not limited thereto, Anyone skilled in the art in the technical scope disclosed by the present invention, according to the technique and scheme of the present invention and its Inventive concept is subject to equivalent substitution or change, should be covered by the protection scope of the present invention.

Claims (7)

1. a kind of novel phosphorescence host compound, it is characterised in that: shown in the structural formula as I of the phosphorescence host compound:
Wherein, L1、L2It is independent to be selected from singly-bound, phenylene, naphthylene；
Z is independently selected from H, C6-C30 aryl, C2-30 heteroaryl；
X is independent to be selected from O, S, Se, NR1、C(R1)2、Si(R1)2, wherein R1Independently selected from hydrogen, C1-C20 substituted or unsubstituted Alkyl, C1-C20 alkoxy substituted or unsubstituted, C6-C30 aryl or C2-C30 heteroaryl.
2. a kind of novel phosphorescence host compound according to claim 1, it is characterised in that: Z independently selected from replace or Unsubstituted having structure:
Wherein, R2、R3、R4Independently selected from hydrogen, C1-C20 alkyl substituted or unsubstituted, C1-C20 alkoxy substituted or unsubstituted, C6-C30 aryl or C2-C30 heteroaryl；
Y1、Y2、Y3Independently selected from C or N.
3. novel phosphorescence host compound according to claim 1, it is characterised in that: the R1Independently selected from following Structure:
4. special according to claim 1 to a kind of novel phosphorescence host compound described in any one of claim 3 claim Sign is: compound of the organic compound independently selected from following structural:
5. a kind of electroluminescent device, including cathode layer, anode layer and organic layer, which includes hole injection layer, hole Transport layer, luminescent layer, hole blocking layer, CPL layers, one or more layers, the feature in electron injecting layer, electron transfer layer It is: contains compound described in claim 1 at least one layer in the organic layer of the device.
6. a kind of electroluminescent device according to claim 5, it is characterised in that: compound described in claim 1 exists Phosphorescent light body material is used as in luminescent layer.
7. a kind of electroluminescent device according to claim 6, it is characterised in that: compound described in claim 1 can To be used alone, or it is used in mixed way with other compounds；It can also be simultaneously using two or more chemical combination in claim 1 Object.
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CN111205295A (en) * 2020-03-04 2020-05-29 西安瑞联新材料股份有限公司 Compound with imidazocarbazole as receptor and application thereof
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